DE241363T1 - NUCLEOSIDE DERIVATIVES AND THEIR USE IN OLIGONUCLEOSIDE SYNTHESIS. - Google Patents

NUCLEOSIDE DERIVATIVES AND THEIR USE IN OLIGONUCLEOSIDE SYNTHESIS.

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Publication number
DE241363T1
DE241363T1 DE198787400739T DE87400739T DE241363T1 DE 241363 T1 DE241363 T1 DE 241363T1 DE 198787400739 T DE198787400739 T DE 198787400739T DE 87400739 T DE87400739 T DE 87400739T DE 241363 T1 DE241363 T1 DE 241363T1
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Germany
Prior art keywords
radical
hydrogen atom
nucleoside derivative
derivative according
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
DE198787400739T
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German (de)
Inventor
Didier F-38120 Tullins Molko
Jean-Claude Montbonnot F-38330 Saint Ismier Schulhof
Robert F-38000 Grenoble Teoule
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Commissariat a lEnergie Atomique et aux Energies Alternatives CEA
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Commissariat a lEnergie Atomique CEA
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Application filed by Commissariat a lEnergie Atomique CEA filed Critical Commissariat a lEnergie Atomique CEA
Publication of DE241363T1 publication Critical patent/DE241363T1/en
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16—Purine radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16—Purine radicals
    • C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Saccharide Compounds (AREA)

Abstract

The derivatives correspond to the formula: <IMAGE> in which B denotes a radical derived from guanine, cytosine or adenine in which the exocyclic NH group is protected by the group <IMAGE> with R<1> denoting a hydrogen atom or an alkyl radical and R<2> denoting a hydrogen atom, an alkyl radical, an alkoxy radical or an optionally substituted aryloxy radical, R<3> denotes a hydrogen atom, the dimethoxytrityl radical or the radical: <IMAGE> R<4> denotes a hydrogen atom, the radical of formula: <IMAGE> or a radical which is suitable for the synthesis of polynucleotides, and R<5> denotes a hydrogen atom or the hydroxyl radical OH, protected or otherwise.

Claims (17)

täSSJLl älißJlL ücJlS.' DE BE FR IT LU NL SE CH + Li GB GR.täSSJLl älißJlL ücJlS.' DE BE FR IT LU NL SE CH + Li GB GR. 1. Nucleosidderivat der Formel1. Nucleoside derivative of the formula (I)(I) worin bedeuten:where: B einen zweiwertigen Rest, gewählt aus:B is a divalent radical selected from: NH HN &Uacgr; ^ (&Pgr;) ; \ I (111) oderNH HN &Uacgr; ^ (&Pgr;) ; \ I (111 ) or der an die CO-Gruppe durch seine exocyclische NH-Gruppe gebunden ist;which is bonded to the CO group through its exocyclic NH group; R ein Wasserstoffatom oder einen Alkylrest;R is a hydrogen atom or an alkyl radical; R ein Wasserstoffatom, einen Alkylrest, Alkoxyrest,R is a hydrogen atom, an alkyl radical, alkoxy radical, Aryloxyrest, nicht substituiert oder substituiert durch eine oder mehrere der Gruppen, gewählt aus NOp/ CN,Aryloxy radical, unsubstituted or substituted by one or more of the groups selected from NOp/ CN, {J{J Alkoxy, Aryloxy, Cl, F, C^ Aw «0 R,Alkoxy, Aryloxy, Cl, F, C^ Aw «0 R, N)R VR 2N)R V R 2 Alkyl oder Aryl, substituiert oder nicht substituiert, SR, worin R einen Alkyl- oder Arylrest bedeutet; mit der Ausnahme von R = H und R = CH-,, wenn B den Rest (II) oder (III) bedeutet und mit Ausnahme von R = R = CH3, wenn B den Rest (II) bedeutet;Alkyl or aryl, substituted or unsubstituted, SR, in which R is an alkyl or aryl radical; with the exception of R = H and R = CH-, when B is the radical (II) or (III) and with the exception of R = R = CH 3 when B is the radical (II); R ein Wasserstoffatom, einen in saurem Milieu labilen Rest oder einen Rest der Formel:R is a hydrogen atom, a residue labile in acidic medium or a residue of the formula: ^CH-CO-^CH-CO- worin R und R die obengenannten Bedeutungen haben;wherein R and R have the meanings given above; 4
R ein Wasser stoff atom, einen phosphorhaltigen Rest oder den Rest:4
R is a hydrogen atom, a phosphorus-containing radical or the radical: CH-CO-R CH-CO-R worin R und R die obengenannten Bedeutungen haben; undwherein R and R have the meanings given above; and R ein Wasserstoffatom oder den Rest OH.R is a hydrogen atom or the residue OH. 2. NucIeosidderivat nach Anspruch 1, dadurch gekennzeichnet, daß der in saurem Milieu labile Rest R gewählt wird aus der Gruppe der Tritylreste der Formel:2. Nucleoside derivative according to claim 1, characterized in that the radical R which is labile in an acidic medium is selected from the group of trityl radicals of the formula: - c- c (V)(V) 6 7 86 7 8 worin R , R und R , die gleich oder verschieden sein können, ein Wasserstoff atom, einen Alkyl- oder Alkoxyrest bedeuten, der Pixylreste und der 9-Phenyl-xanthenyl-Reste,where R , R and R , which may be the same or different, are a hydrogen atom, an alkyl or alkoxy radical, the pixyl radicals and the 9-phenyl-xanthenyl radicals, 3. Nucleosidderivat nach einem der Ansprüche 1 und 2, dadurch gekennzeichnet, daß der phosphorhaltige Rest R gewählt wird aus der Gruppe der Reste der Formel:3. Nucleoside derivative according to one of claims 1 and 2, characterized in that the phosphorus-containing radical R is selected from the group of radicals of the formula: Osp-0 «Osp-0 « (VI)(VI) der Formel:the formula: NCCH CH 0-P-NNCCH CH 0-P-N CHCH CHCH CHCH \ CH\ CH CHCH (VII)(VII) KJ Cm-T I V/W KJ Cm-T IV/W ,1 f (? f f t · * '(T; >,1 f (? f f t · * '(T; > oder der Formel:or the formula: H-P-OH-P-O 4. NucLeosidderivat nach Anspruch 1, dadurch gekennzeichnet, daß B den Rest:4. Nucleoside derivative according to claim 1, characterized in that B is the radical: (II)(II) bedeutet;means; R ein Wasserstoffatom bedeutet undR represents a hydrogen atom and R einen ALkoxyrest oder AryI oxy rest, der gegebenenfalls substituiert ist, bedeutet.R represents an alkoxy radical or an aryloxy radical which is optionally substituted. 5. Nucleosidderivat nach Anspruch U, dadurch gekennzeichnet, daß R ein Rest ist, gewählt aus:5. Nucleoside derivative according to claim U, characterized in that R is a radical selected from: oder CH3O-or CH 3 O- «ft * *«ft * * 6. Nucleosidderivat nach Anspruch 1, dadurch gekennzeichnet/ daß B den Rest:6. Nucleoside derivative according to claim 1, characterized in that B is the radical: bedeutet;means; R ein Wasser stoff atom bedeutet undR is a hydrogen atom and R einen gegebenenfalls substituierten Aryloxyrest bedeutet.R represents an optionally substituted aryloxy radical. 7. Nucleosidderivat nach Anspruch 6, dadurch gekennzeichnet, daß R den Phenoxyrest bedeutet7. Nucleoside derivative according to claim 6, characterized in that R is the phenoxy radical 8. Nucleosidderivat nach Anspruch 1, dadurch gekennzeichnet, daß B den Rest:8. Nucleoside derivative according to claim 1, characterized in that B is the radical: (III)(III) bedeutet;means; R und R , die gleich oder verschieden sein können, ein Wasserstoff atom oder einen Alkylrest bedeuten.R and R , which may be the same or different, represent a hydrogen atom or an alkyl radical. 9. Nucleosidderivat nach Anspruch 8, dadurch9. Nucleoside derivative according to claim 8, characterized 1 2 gekennzeichnet, daß R und R den Methylrest bedeuten.1 2 characterized in that R and R represent the methyl radical. # e · 4# e · 4 10. Nucleosidderivat nach einem der Ansprüche 1 und10. Nucleoside derivative according to one of claims 1 and 3 4 4 bis 9, dadurch gekennzeichnet, daß R und R3 4 4 to 9, characterized in that R and R ein Wasserstoffatom bedeuten.a hydrogen atom. 11. NucLeosidderivat nach einem der Ansprüche 1 und 4 bis 9/ dadurch gekennzeichnet, daß R den Rest:11. Nucleoside derivative according to one of claims 1 and 4 to 9 / characterized in that R is the radical: - C- C OCH. OCH.OCH. OCH. und R ein Wasserstoff atom bedeuten.and R represents a hydrogen atom. 12. NucLeosidderivat nach einem der Ansprüche 1 bis 11, dadurch gekennzeichnet, daß R ein Wasserstoffatom bedeutet12. Nucleoside derivative according to one of claims 1 to 11, characterized in that R represents a hydrogen atom 13. NucLeosidderivat nach einem der Ansprüche 1 und 4 bis 9, dadurch gekennzeichnet, daß R den Rest:13. Nucleoside derivative according to one of claims 1 and 4 to 9, characterized in that R is the radical: - C- C OCH. OCH.OCH. OCH. «A b * * * U 4 «A b * * * U 4 &igr; &lgr; * &igr; u *- i <&igr;&lgr; * &igr; u *- i < und R den Rest:and R the rest: &Lgr; I C-) &Lgr; I C-) O = P-OO = P-O 0 C H Cl0 C H Cl bedeuten.mean. 14. Nucleosidderivat nach einem der Ansprüche 1 und 4 bis 9, dadurch gekennzeichnet, daß R den Rest:14. Nucleoside derivative according to one of claims 1 and 4 to 9, characterized in that R is the radical: - C- C OCH, OCH.OUCH, OUCH. und R den Rest:and R the rest: NCCH CH 0-&Rgr;-&Ngr;NCCH CH 0-&Rgr;-&Ngr; CHCH (VIX)(VIX) bedeuten.mean. 15. Nucleosidderivat nach einem der Ansprüche 1 und 4 bis 9, dadurch gekennzeichnet/ daß R den Rest:15. Nucleoside derivative according to one of claims 1 and 4 to 9, characterized in that R is the radical: - C- C 4 und R den Rest:4 and R the rest: Il (-) <&diams;)Il (-) <&diams;) -P-O (C H ) NH I 2 5 3-P-O (C H ) NH I 2 5 3 bedeuten.mean. 16. Nucleosidderivat nach einem der Ansprüche 13 bis 15, dadurch gekennzeichnet, daß R ein Wasser stoff atom bedeutet.16. Nucleoside derivative according to one of claims 13 to 15, characterized in that R represents a hydrogen atom. 17. Verfahren zur Herstellung von OligonucIeotiden, dadurch gekennnzeichnet, daß es umfaßt:17. Process for the preparation of oligonucleotides, characterized in that it comprises: 1) mindestens einen Kondensationszyklus, bei dem man auf ein Nucleosidderivat oder auf ein Oligonucleotid ein Nucleosidderivat der folgenden Formel kondensiert:1) at least one condensation cycle in which a nucleoside derivative of the following formula is condensed onto a nucleoside derivative or onto an oligonucleotide: (I)(I) worin bedeuten:where: B einen zweiwertigen Rest, gewählt aus:B is a divalent radical selected from: (III)(III) (IV)(IV) der an die Gruppe CO durch seine exocyclische NH-Gruppe gebunden ist;which is bonded to the CO group through its exocyclic NH group; ein Wasserstoffatom oder einen AlkyLrest;a hydrogen atom or an alkyl radical; ein Wasserstoffatom, einen Alkylrest, Alkoxyrest, Aryloxyrest, nicht substituiert oder substituiert mit einer oder mehreren der Gruppen gewählt aus NO2, CN, Alkoxy, Aryloxy, Cl, F, &khgr;&Ogr; a hydrogen atom, an alkyl radical, alkoxy radical, aryloxy radical, unsubstituted or substituted with one or more of the groups selected from NO 2 , CN, alkoxy, aryloxy, Cl, F, &khgr;&Ogr; ,C' , SO R, S , &PSgr;* , ^R 2 ^R ^ (OR) 2 , Alkyl oder,C' , SO R, S , &PSgr;* , ^R 2 ^R ^ (OR) 2 , alkyl or Aryl, substituiert oder nicht substituiert, SR, worin R einen Alkyl- oder Arylrest bedeutet,Aryl, substituted or unsubstituted, SR, wherein R is an alkyl or aryl radical, wenn Bif B mit Ausnahme von R = H und R = CHwith the exception of R = H and R = CH den Rest (II) oder (III) bedeutet und mit Ausnahmethe remainder (II) or (III) and with the exception 3'3' von R=R= CH,, wenn B den Rest (II) bedeutet;of R=R= CH,, when B represents the radical (II); einen in saurem Milieu labilen Rest;a residue that is labile in acidic environments; R einen phosphorhaltigen Rest undR is a phosphorus-containing radical and R ein Wasser stoff atom; undR is a hydrogen atom; and t, h -j &iacgr; 6t, h -j &iacgr; 6 2) eine Stufe der Elimination einer oder mehrerer Schutzgruppen der Formet:2) a step of elimination of one or more protecting groups of the formula: CH-CO-RCH-CO-R worin R und R wie oben definiert sind,where R and R are as defined above,
DE198787400739T 1986-04-08 1987-04-03 NUCLEOSIDE DERIVATIVES AND THEIR USE IN OLIGONUCLEOSIDE SYNTHESIS. Pending DE241363T1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR8604990A FR2596761B1 (en) 1986-04-08 1986-04-08 NUCLEOSIDE DERIVATIVES AND THEIR USE FOR SYNTHESIS OF OLIGONUCLEOTIDES

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DE241363T1 true DE241363T1 (en) 1988-06-30

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DE8787400739T Expired - Lifetime DE3773245D1 (en) 1986-04-08 1987-04-03 NUCLEOSIDE DERIVATIVES AND THEIR USE IN OLIGONUCLEOSIDE SYNTHESIS.
DE3751947T Expired - Lifetime DE3751947T2 (en) 1986-04-08 1987-04-03 Nucleoside derivatives and their use in oligonucleotide synthesis
DE198787400739T Pending DE241363T1 (en) 1986-04-08 1987-04-03 NUCLEOSIDE DERIVATIVES AND THEIR USE IN OLIGONUCLEOSIDE SYNTHESIS.

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DE3751947T Expired - Lifetime DE3751947T2 (en) 1986-04-08 1987-04-03 Nucleoside derivatives and their use in oligonucleotide synthesis

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US (1) US4980460A (en)
EP (2) EP0438203B1 (en)
JP (2) JPH0631305B2 (en)
AT (1) ATE67768T1 (en)
DE (3) DE3773245D1 (en)
ES (1) ES2001000A4 (en)
FR (1) FR2596761B1 (en)
GR (1) GR880300040T1 (en)

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ATE67768T1 (en) 1991-10-15
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DE3773245D1 (en) 1991-10-31
EP0241363B1 (en) 1991-09-25
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DE3751947T2 (en) 1997-05-07
JPH0631305B2 (en) 1994-04-27
ES2001000A4 (en) 1988-04-16
US4980460A (en) 1990-12-25
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EP0438203B1 (en) 1996-11-06
JPS62294692A (en) 1987-12-22
FR2596761B1 (en) 1988-05-20

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